Chemistry

Haloalkanes and Haloarenes

Question:

Alkyl halides are prepared from alcohol by treating with
(a) HCl + ZnCl2     (b) RedP + Br2
(c) H2SO4 + KI    (d) all the above

Answer:

ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-45

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Haloalkanes and Haloarenes

Q 1.

Write the isomers of the compound having formula C4H9Br.

Q 2.

Match the structures of compounds given in Column I with the classes of compounds given in Column II.
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-84

Q 3.

Draw the structures of major monohalo products in each of the following reactions:
ncert-class-12-solutions-chemistry-chapter-10-haloalkanes-haloarenes-5

Q 4.

Chloromethane on treatment with excess of ammonia yields mainly
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-26

Q 5.

How will you bring about the following conversions?
(i)Ethanol to but-l-yne . (ii)Ethane to bromoethene
(iii)Propene to 1-nitropropane (iv)Toluene to benzyl alcohol
(v)Propene to propyne (vi)Ethanol to ethyl fluoride
(vii)Bromomethane to propanone (viii)But-l-ene to but-2-ene
(ix)1-Chlorobutane to n-octane (x)Benzene to biphenyl

Q 6.

Chlorobenzene is formed by reaction of chlorine with benzene in the presence of AlCl3. Which of the following species attacks the benzene ring in this reaction?
(a) CP     (b) Cl+   (c) AlCl3     (d) [AlCl4]

Q 7.

Elimination reactions (especially Beta-elimination) are as common as the nucleophilic substitution reaction in case of alkyl halides. Specify the reagents used in both cases.

Q 8.

Which of the following compounds will give racemic mixture on nucleophilic substitution by OH ion?
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-31

Q 9.

Alkyl halides are prepared from alcohol by treating with
(a) HCl + ZnCl2     (b) RedP + Br2
(c) H2SO4 + KI    (d) all the above

Q 10.

Match the items of Column I and Column II.
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-83

Q 11.

In which of the following molecules carbon atom marked with asterisk (*) is
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-13

Q 12.

Ethylene chloride and ethylidene chloride are isomers. Identify the correct statements.  
(a) Both the compounds form same product on treatment with alcoholic KOH
(b) Both the compounds from same product on treatment with aqueous NaOH
(c) Both the compounds form same product on reduction
(d) Both the compounds are optically active

Q 13.

How do polar solvents help in the first step in SN1 mechanism?

Q 14.

Which of the products will be major product in the reaction given
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-53

Q 15.

What are the IUPAC name of the insecticide DDT and benzenehexachloride?
Why is their use banned in India and other countries?

Q 16.

Which of the following are secondary bromides?
(a) (CH3),CHBr     (b) (CH3)3C CH2Br
(c) CH3CH(Br)CH2CH3     (d) (CH3)2CBrCH2CH3

Q 17.

Diphenyls are potential threat to the environment. How are these produced from arylhalides?

Q 18.

Some alkylhalides undergo substitution whereas some undergo elimination reaction on treatment with bases. Discuss the structural features of alkyl halides with the help of examples which are responsible for this difference.

Q 19.

Out of C6H5CH2Cl and C6H5CHCIC6H5which is more easily hydrolysed by aqueous KOH.

Q 20.

Which of the following statements are correct about the reaction intermediate?
(a) Intermediate (iii) is unstable because in this carbon is attached to 5 atoms.
(b) Intermediate (iii) is unstable because carbon atom is sp2 hybridised.
(c) Intermediate (iii) is stable because carbon atom is sp2 hybridised.
(d) Intermediate (iii) is less stable than the reactant (ii).

Q 21.

How will you obtain monobromobenzene from aniline?

Q 22.

Which compound in each of the following-pairs . will react faster in SN2 reaction with -OH? (i)CH3Br or CH3I
(ii)(CH3)3CCl or CH3Cl

Q 23.

Which of the carbon atoms present in the molecule given below are asymmetric?
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-30

Q 24.

Which of the following statements are correct about the kinetics of this reaction?
(a) The rate of reaction depends on the concentration of only (ii).
(b) The rate of reaction depends on concentration of both (i) and (ii).
(c) Molecularity of reaction is one.
(d) Molecularity of reaction is two.

Q 25.

Write the structures and names of the compounds formed when compound ‘A' with molecular formula, C7H8 is treated with Cl2 in the presence of FeCl3.

Q 26.

Which alkyl halide from the following pairs would you expect to react more rapidly by an SN2 mechanism? Explain your answer.
ncert-class-12-solutions-chemistry-chapter-10-haloalkanes-haloarenes-7
ncert-class-12-solutions-chemistry-chapter-10-haloalkanes-haloarenes-8

Q 27.

Arrange the following compounds in the increasing order of their densities Cl
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-10

Q 28.

Which of the following compounds (a) and (b) will not react with a mixture of NaBr and H2S04. Explain why?
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-51

Q 29.

Assertion (A): tert-Butyl bromide undergoes Wurtz reaction to give 2, 2, 3, 3-tetramethylbutane.
Reason (R): In Wurtz reaction, alkyl halides react with sodium in dry ether to give hydrocarbon containing double the number of carbon atoms present in the halide.

Q 30.

Assertion (A): Nitration of chlorobenzene leads to the formation of m-nitrochlorobenzene.
Reason (R): N02 group is a w-directing group.

Q 31.

Write the equations for the preparation of 1-iodoobutanefrom (i)1-butanol (ii)1-chlorobutane (iii) but-l-ene.

Q 32.

Which of the following is halogen exchange reaction?
(a)
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-7

Q 33.

Questions on the basis of the following reaction:
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-38

 Which of the following statements are correct about the mechanism of this reaction?
(a) Acarbocation will be formed as an intermediate in the reaction.
(b) OH will attach the substrate (iii) from one side and Cl will leave it simultaneously from other side.
(c) An unstable intermediate will be formed in which OH  and Cl will be attached by weak bonds.
(d) Reaction proceeds through SN1 mechanism.

Q 34.

Which of the following compounds can be classified  as aryl  halides ? (a) p-ClC6H4CH2CH(CH3)2 (b) p-CH3CHCl(C6H4)CH2CH3  (c) o-BrH2CC6H4CH(CH3)CH2CH3 (d) C6H5Cl

Q 35.

Which of the compounds will react faster in SN1 reaction with the OH ion?
CH3 – CH2 – Cl or C6H5 – CH2 – Cl

Q 36.

Why is the solubility of haloalkanes in water very low?

Q 37.

Discuss the nature of C – X bond in the haloarenes.
C – X bond in haloarenes is extremely less reactive towards nucleophilic

Q 38.

How can you obtain iodoethane from ethanol when no other iodine containing reagent except Nal is available in the laboratory?

Q 39.

Cyanide ion acts as an ambident nucleophile. From which end it acts as a stronger nucleophile in aqueous medium? Give reason for your answer.

Q 40.

Assertion (A): The boiling points of alkyl halides decrease in the order: RI > RBr > RCl > RF
Reason (R): The boiling points of alkyl chlorides, bromides and iodides are considerably higher than that of the hydrocarbon of comparable molecular mass.

Q 41.

Assertion (A): KCN reacts with methyl chloride to give methyl isocyanide Reason (R): CN–  is an ambident nucleophile.

Q 42.

Assertion (A): It is difficult to replace chlorine by -OH in chlorobenzene in comparison to that in chloroethane.
Reason (R): Chlorine-carbon (C – Cl) bond in chlorobenzene has a partial double bond character due to resonance.

Q 43.

Write structures of the following compounds:
(i) 2-Chloro-3-methylpentane
(ii) 1-Chloro-4-ethylcydohexane
(iii) 4-tert. Butyl-3-iodoheptane
(iv) 1,4-Dibromobut-2-ene
(v) 1-Bromo-4-sec. butyl-2-methylbenzene.

Q 44.

Write structures of different dihalogen derivatives of propane.

Q 45.

Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides:
(i)(CH3)2CHCH(Cl)CH3
(ii) CH3CH2CH(CH3)CH(C2H5)CI
(iii) CH3CH2C(CH3)2CH2I
(iv)(CH3)3CCH2CH(Br)C6H5
(v)CH3CH(CH3)CH(Br)CH3
(vi)CH3C(C2H5)2CH2Br
(vii)CH3C(Cl)(C2H5)CH2CH3
(viii)CH3CH=C(CI)CH2CH(CH3)2
(ix)CH3CH=CHC(Br)(CH3)2
(x)P-CIC6H4CH2CH(CH3)2
(xi)m-ClCH2C6H4CH2C(CH3)3
(xii)o-Br -C6H4CH (CH3)CH2CH3

Q 46.

The order of reactivity of following alcohols with halogen acids is
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-1

Q 47.

Which of the following alcohol will yield the corresponding alkyl chloride on reaction with concentrated HCl at room temperature?
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-3

Q 48.

Which reagent will you use for the following reaction?
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-8

Q 49.

Which of the following structure is enantiomeric with the molecule (A) given below:
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-14

Q 50.

ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-33